Fluorine-containing alkyl iodides have a broad range of applications as ingredients for producing a variety of products such as surfactants, pharmaceuticals, functional polymers, etc.
In particular, compounds obtained by an ethylene addition reaction between the iodine atom and the polyfluoro alkyl group of polyfluoroalkyl iodides (such compounds are hereinafter referred to as polyfluoroalkylethyl iodides) can be converted to various other compounds since the iodine therein can be more readily substituted by a nucleophile compared with the iodine contained in polyfluoroalkyl iodides. Therefore, polyfluoroalkylethyl iodides have drawn attention as ingredients for a broad range of products.
As an example of a process for producing such polyfluoroalkylethyl iodides, a process employing an ethylene addition reaction to polyfluoroalkyl iodides (hereinafter simply referred to as an “ethylene addition reaction”) as shown below is known:Rf—I+CH2═CH2→Rf—CH2CH2—Iwherein Rf is a C1-6 polyfluoroalkyl.
In connection with such ethylene addition reactions, processes employing ruthenium/activated carbon (Ru/C), platinum/activated carbon (Pt/C), silver/alumina (Ag/Al2O3) and like noble metals as catalysts (Konrad von Werner, Journal of Fluorine Chemistry 28(1985): 229–233); processes employing azobisisobutyronitrile (AIBN) or benzoyl peroxide and like organic peroxides as catalysts (Neal O. Brace, Journal of Fluorine Chemistry 93(1999): 1–25); etc., have been reported. However, noble metals have the disadvantage that they are expensive and thus result in high production costs. Organic peroxides are also expensive and for one-time use only, resulting in high production costs. Furthermore, organic peroxides are disadvantageous in that they are hazardous per se and cause inclusion of impurities in the reaction product. Meanwhile, ethylene addition reactions conducted in the presence of metallic copper catalysts have not been reported.
As an example of a process for producing starting material polyfluoroalkyl iodides, the telomerization reaction conducted in the presence of a copper catalyst as shown below (hereinafter simply referred to as a “telomerization reaction”) is known (Japanese Unexamined Patent Publication No. 239336/1996; Qing-Yun Chen, et al., Journal of Fluorine Chemistry 36(1987): 483–489; etc.):Rf—I+nCF2═CF2→Rf(CF2CF2)nIwherein Rf is a C1-6 polyfluoroalkyl and n is an integer from 1 to 8.
It has not been reported that such a telomerization reaction and the aforementioned ethylene addition reaction can be successively conducted using the same catalyst. If these reactions can be successively conducted in the presence of the same catalyst, simplification of the production process and reduction in production cost are to be expected.